Chloro-iodides of 2-amino-pyridin-salts and process of making same



Patented Aug. 6, 1929.

UNITED STATES PATENT OFFICE.

MAX DOHRN AND RALZH DIRKSEN, OF BERLIN-CHARLOTTENBURG. GERMANY, AS-

SIGNQBS TO THE FIRM CHEMISCHE FABRIK AUF ACTIEN (VORM E. SCHERINGJ,

OF BERLIN, GERMANY.

CHLOROIODIDES OF 2=-lAMINO-PYRIDIN-SALTS AND PROCESS OF MAKING SAME.

NoDrawing. Application filed January 5, 1927, Serial No. 159,241, and in Germany January 15, 1926.

Our invention refers to new products re sulting from the interaction of -a-am1no pyridin and its derivatives with iodine chloride compounds and to the method of pro- 5 ducing same, the products being useful in the production of medical preparations,

We have ascertained that if iodine chloride is allowed to act in acid solution on a-ll1lll10 pyridin and its derivatives, there are formed 30 precipitates which are insoluble in acids and which are salts of the iodine'chloride compounds of a-amino pyridin or its derivatives. In the majority of cases these salts are well crystallized and substantially stable.

They are not decomposed when boiled in acid solution and, on cooling such solution separate out under the form of crystals.

All these compounds are capable of forming in alkaline solution the corresponding B-iodine derivatives of the base.

E :rample 1.

5, 8 grams oc-2L111ln0 pyridin are dissolved in 40 c c dilute hydrochloric acid and a solution of 10 grams iodine'chloride in 20 c c dilute hydrochloric acid is added, whereupon the hydrochloride of the iodine chloride compound of wamino pyridin Willseparate out in beautiful needles melting at 141, these needles being the color of lemon yellow. The compound has the formula the melting point of 155. The compound has the formula /NH-OO-CH3QHCI Example 3. 5o 7, 6 grams a-ethyl amino pyridin, when treated as described with reference to- Example 1, result in a compound melting at 90-91. The compound has the formula mula O/NH- oncum-11o:

Example 5.

10 grams wisoamyl amino pyridin which is obtained from oL-flllllllO pyridin sodium and isoamyl bromide), when treated in accordance with Example 1, yield a crystallizing compound melting at -51 The compound has the formula Example 6'. a-diethyl amino pyridin, if treated as described with reference to Example 1, yields the hydrochloride of the iodine chloride compound melting at 5455. It has the formula ple 1 result in a product melting at 105106 It has the formula Other salts can be obtained in an analogous manner.

Various changes may be made in the details of the operation and particularly in the proportions of the ingredients present in the solutions without departing from the invention or sacrificing the advantages thereof. We claim 1. As a new product, a salt of the iodinechloride compound of a-anlino pyridin having the formula t NJLY 1 I in which X=H or alkyl, Y=H or alkyl or acyl, and wherein free positions of the pyridin nucleus can be substituted as well, such salts being as a rule crystallized and substantially stable even when boiled in acid solution from which they segregate on cooling in the form of crystals, the compounds being capable of being transformed in alkaline solu- I W NH- Call" such salt being crystallized and substantially stable and having a melting point of 505l 6., the compound being capable of being transformed in alkaline solution with a good yield into the B-iodine derivative.

The method of producing iodine chloride compounds of a-amino pyridin and its derivatives comprising treating the raw ma terial with iodine chloride in acid solution.

4. The method of producing the iodine chloride compound of a-isoamyl amino pyridin comprising treating a solution of parts by weight a-isoamyl aminopyridin in about 40 parts dilute hydrochloric acid with a solution of 10 parts iodine chloride in about parts dilute hydrochloric acid.

In testimony whereof we afiix our signatures.

' MAX DOHRN.

RALPH DIRKSEN. 

